The 10 Worst Outfits First Ladies Have Been Caught Wearing

The role of the First Lady of the United States has evolved over the years. In addition to overseeing domestic affairs in the White House, it now includes public-facing social duties, such as leading campaigns that support veterans and creating initiatives focused on the wellness of children nationwide. Beyond these important causes, First Ladies have played a crucial part in influencing the world of fashion.

Former FLOTUS Michelle Obama's style, for instance, featured off-the-rack clothes that were readily available to the public and often sold out quickly. Impressively, a study by David Yermack, a professor of finance and business transformation at New York University's Stern School of Business, showed that Obama helped publicly traded clothing companies make up to $2.7 billion in sales (via ABC News) as of November 2010.

First ladies' outfits have been so influential that over the years, the Smithsonian's National Museum of American History has showcased their gowns in various exhibitions. Even though some of their past looks have been head-turning, like the rare times Melania Trump pulled off a pantsuit better than Kamala Harris, sometimes our favorite first ladies just fell short of the mark. We've seen them wearing outfits that were culturally insensitive, pairing chic looks with mismatched shoes, and in some instances, simply choosing the wrong accessories.

When President Donald Trump was serving his first term in office, First Lady Melania Trump embarked on her first official solo trip overseas to Kenya in October 2018. Her itinerary included a tour of the Nairobi National Park, during which she spent time at the Sheldrick Elephant Orphanage and went on a safari, a visit to the Nest Children's Home, a private meeting with the then Kenyan First Lady, Margaret Kenyatta, at the State House, and a U.S. embassy courtesy call.

While Melania was impressed by her diplomatic mission, telling the White House that "the hospitality that I received made the experience so special," her visit wasn't without a major wardrobe controversy. While on safari, Melania was pictured in a crisp, button-down, collared white shirt paired with a set of beige pants and calf-high boots. The First Lady's look suited the occasion, but a wide-brimmed white pith helmet she wore to shield herself from the scorching sun caused an uproar on social media due to its connection to British colonialism.

"I wonder why she is trying to offends [sic] her hosts? She can't be that tacky & insensitive can she?" One critic wrote on X. While some of the social media platform's users felt that the backlash Melania received was unwarranted, others used the moment to educate the public on the helmet's history. "Military berets were first worn by the French in 1889 and date back to ancient Rome, as well as Etruscans and Minoans," one such user wrote (via X).

Former First Lady Dr. Jill Biden has been caught in some outfits that missed the mark, but none caused as much of a frenzy as when she wore an all-black ensemble in April 2021. Biden was pictured exiting Air Force One in a chic look featuring a cozy blazer, an A-line skirt, and ankle-length boots. She paired the outfit with patterned lacy tights that were quite popular back in the '60s (they have since made a comeback since December 2024).

Several online users felt that Biden was trying too hard to achieve a youthful look, while some expressed that her choice displayed a lack of class. Other critics voiced that the fashion fail was a poor representation of the Bidens' leadership, writing (via X), "OMG, just awful! No wonder other countries feel they can tell us what to do. Such a disappointment." A lot of confusion also arose on whether Biden was wearing a fishnet, and as it turned out, she wasn't.

Of course, Biden herself saw no fault in her appearance. The former FLOTUS told Vogue in a later interview, "They were very pretty stockings." Biden also expressed her astonishment at how the public watched her, like a hawk. "It's amazing how much people pay attention to every little detail," she told the outlet.

Former President Barack Obama made history by becoming the first African-American president when he was elected to office in November 2008, but he and his family had hardly settled in the White House when Michelle Obama was subjected to her first major fashion faux pas. For her first official photo as First Lady, Michelle donned a sleeveless black Michael Kors dress that she accessorized with vibrant white pearls and a broad smile. On any other day, the look would have been welcome, but Michelle showed her most controversial asset yet: her bare arms.

Most critics felt that Michelle's look was too easy-going, while others opined that her choice didn't blend in with the season at the time: winter. Those who took to Michelle's defense argued that the backlash was a result of intimidation, all while some opinion pieces suggested that it could have been a representation of underlying racism and sexism issues. Some loyalists later pitted Michelle against First Lady Melania Trump, asserting that bare arms were a non-issue in comparison to posing in the nude (Melania's professional modeling pictures from a nude photo shoot with British Vogue have often made headlines).

When she finally responded to the negative comments long after she had left the White House, Michelle dismissed the reactions to her photo as political play. "I took it for what it was. It was pure hypocrisy," she told People. "I was just straight up kind of ... do you not look at history? ... At a point you're like, 'Oh ... this is politics.' If you can't beat 'em, make everybody scared of 'em."

Following Former President Bill Clinton's election to office in November 1992, he and Former First Lady Hillary Clinton hosted their first state dinner at the National Governors Association winter meeting. The January 1993 event featured attendances by several prominent figures, including the then Vice President, Albert Gore Jr. Hillary cemented her name in history books for her fashion choice of the night, a long-length, figure-hugging dress by designer Donna Karan.

The alluring cold-shoulder number featured a high neck, full sleeves, and shoulder cut-outs that controversially made Hillary the talk of the town. Some critics argued that making a fashion headline at the time was confusing because Hillary hadn't properly established her identity (she was previously the First Lady of Arkansas and had worked extensively with families and children in her role). Bill had just appointed Hillary to head his Task Force on National Health Reform on January 25, 1993, and critics had questions on whether she was a health icon, a fashion trendsetter, or the perfect White House host.

Speaking on the ensuing controversy in a chat with Lenny Letter years later, Hillary said, "I thought it would be fun ... You've got to still have fun in all these different roles you're in or I'm in or anybody is in their life." The cold-shoulder dress was arguably ahead of its time since it eventually became a runway favorite, featuring in party dresses, streetwear, and even minimalist clothing.

Laura Bush was First Lady from 2001 to 2009, and when it comes to fashion, she kept things simple and elegant. In her 2010 memoir, "Spoken from the Heart," Bush wrote that living under the watchful eye of fashion critics was difficult because she wasn't one to keep up with trends. Bush, who maintained that her wardrobe budget wasn't accounted for by the government, had her fair share of fashion flops.

One of her biggest blunders was in December 2006, when she wore an off-the-rack Oscar de la Renta gown to the White House reception for the Kennedy Center Honors. The former First Lady looked sophisticated in a lacy red number with long sleeves and a mandarin collar, which was reported to have set her back a cool $8,500. Unfortunately for Bush, three other women at the event had shown up in the same gown, and as such, she had to change into a different outfit.

Bush's camp brushed off the incident as a minor fashion misstep, especially since she and the late designer shared an endearing relationship (de la Renta had previously dressed Bush in numerous stunning looks, including a chic winter white coat she wore to the 2005 inaugural parade). "Evidently, Oscar is very popular this season," Bush's press secretary, Susan Whitson, told the media at the time (via the New York Post). "It just goes to show that no one can resist a beautiful red gown."

On New Year's Eve 2023, Former President Joe Biden and Former FLOTUS Jill Biden made an appearance on "Dick Clark's New Year's Rockin' Eve with Ryan Seacrest." Looking cheerful as ever, Joe dished out details on his preferred holiday cuisine, his highlights and best memories from 2023, and delivered a message of hope to the country.

On her part, the ever-supportive Jill encouraged citizens to be optimistic and kind, and although her words were welcome, the same could not be said for her outfit. Jill wore a short-sleeved sheer black number that she paired with drop earrings. The dress featured a transparent neckline and multicolored flower details, which a lot of fashion critics found to be visually overwhelming. It was likened to things like drapes and fruitcake, and according to one X user, resembled "left over wrapping paper."

The look was nothing like Jill's usual holiday style, as she had previously made appearances on the television show with more fashionable outfits. On New Year's Eve 2020, Jill looked elegant in a long-sleeved green velvet and leather number, and two years later, she kept her appearance vibrant with a long-sleeved purple top that featured multiple cutouts.

President Donald Trump and his wife, First Lady Melania Trump, went on a state visit to the United Kingdom in September 2025. The First Lady's itinerary included a tour of the Royal Library and a meeting with the joint president of the Scout Association, which made for great news, but she truly stirred up a buzz for her fashion choices during a meeting with King Charles and Queen Camilla.

In one picture, Melania was seen in a well-tailored purple skirt suit, featuring a wide-brimmed hat that hid her face. The look caused havoc online, but things got worse when Melania later showed up to a state banquet in a long-length yellow Carolina Herrera gown that was considered another fashion flop (Melania is no stranger to wearing inappropriate outfits). The long-sleeved, off-shoulder dress had a slit that made it look a bit off and was accessorized with a pink belt that left visible bumps under the fabric.

One online critic took to X to disapprove of the ensemble, writing in part, "I usually love love love whatever Melania is wearing, but not today. The color, cut and the belt of the gown was a complete miss. (And from my favorite designer!)" The same critic also voiced that Melania's earrings — a pair of emerald double drop pieces with golden detail — were a good choice that just didn't match that particular outfit.

Former First Lady Hillary Clinton made headlines in 2016 for wearing well-tailored pantsuits in various colors, but before they became her go-to look, she made some significant fashion mistakes. One of those times was when she and Former President Bill Clinton paid a state visit to Japan in April 1996. The then-first family's itinerary included dinner with Japan's Prime Minister, Ryutaro Hashimoto, during which Hillary sported a black suit.

Hillary was pictured in black several times — while exiting the plane, at a state dinner, and during a visit to a Chrysler dealership alongside Bill. On any given day, her choice of wardrobe wouldn't be subject to criticism, but in this case, it set tongues wagging because the color black is associated with somber moods like funerals. Not that it does not have other meanings in Japan; black shows enlightenment when worn by priests and is a symbol of masculinity that is part of men's wedding outfits.

Many assumed that Hillary may have been grieving since the Clinton administration lost its Secretary of Commerce, Ron Brown, to a plane crash in Croatia on April 3, 1996. That claim was denied by her spokesperson, who told the press (via The Washington Post), "She [Hillary] is not in mourning."

Michelle Obama has been caught wearing one too many inappropriate outfits, and that includes the time she made headlines for stepping out of Air Force One in a pair of shorts. During the August 2009 mishap, the former FLOTUS was pictured in dark gray shorts and a fitting white tank top. Michelle added a pop of color to the look with a short-sleeved, checked, pastel green shirt and crowned it with a pair of sneakers and dark sunglasses.

The Obamas were on a family vacation at the Grand Canyon National Park in Arizona, but most critics opined that Michelle's choice was unprecedented. In fact, the move was seen as a disrespect to the presidency. The exact outfit that's appropriate for such a trip remains unclear, but when former First Lady Jill Biden later visited the famous park, she wore a dress and sneakers.

In a later interview with BET's "106 & Park," Michelle agreed that the fashion faux pas was her worst one yet. "I kind of always am happy with what I'm wearing," she told the outlet when asked about her biggest regret. "Sometimes as First Lady, sometimes I forget I'm the First Lady and I'm running around in shorts." 

Melania Trump has worn several outfits that missed the mark, and her choice of stilettos during an August 2017 visit to Texas was no exception. America was saddened when Hurricane Harvey hit the southern state at the time, and as well-wishers made donations to help those who were affected by the floods, Melania and Donald Trump, who were serving his first term, were pictured on their way to offer their support. While Donald's outfit was fit for the occasion (he wore a pair of khaki pants, a light jacket, and tough footgear), Melania's look wasn't quite right.

Melania was dressed in an all-black ensemble featuring a set of pants and a shirt, which she styled with a jungle green bomber jacket. Melania's sunglasses added a casual twist to the outfit, but it was her inclusion of high-heeled, closed-toe shoes to the look that really rubbed online critics the wrong way. The shoes weren't fit for a flood zone.

Some critics used the opportunity to make digs at President Donald, writing (via X), "You won't let her go out unless she looks a certain way ... We all know what women are to you. Subjects to be controlled." Melania later changed into more appropriate footwear when she finally landed in Texas. While addressing the controversy afterward, Donald claimed that Melania had worn the pumps "because we respect the White House a lot," as CNN reported.